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Sherwood started making films in Super 8 at the age of 11. His first films were based on the classic Gothic horror films of Universal, but as he explored cinematic possibilities, his films became more aesthetically daring, going from titles such as Return of Frankenstein to ones such as The Sins of the Children and My Plastic Sweetheart. Soon he was making sound films in high school that were as long as an hour in length. After winning a prize at the New River Mixed Media Gathering for his short film My Love, he moved on to study Broadcasting-Cinema at the University of North Carolina, then receive a Bachelor of Arts in Cinema & Photography at Southern Illinois University as well as a Master of Fine Arts degree at Ohio University. During this time, he won the annual student editing competition conducted by the American Cinema Editors, as well as won a Student Academy Award, Narrative Category, for his masters' thesis film, The Projectionist. He ventured into the film industry in post production, serving as editor, assistant editor, and post production supervisor on many feature films. During it all, he has maintained his own personal filmmaking activities. He has given numerous presentations about film, and has been an active member of Toastmasters International, where he has received numerous speaking awards.